73493-56-8Relevant articles and documents
Stereochemistry of hydrogen loss on formation of the vinyl group in the biosynthesis of ravidomycin
Robert F. Keyes,David G.I.Kingston
, p. 6127 - 6129 (1989)
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Characterisation of the citrate synthase reaction with propionyl-CoA.
Brand?nge,Josephson,M?hlén,M?rch
, p. 695 - 700 (2007/10/02)
Experiments with propionyl-CoA stereoselectively deuteriated in the propionyl moiety demonstrate that the formation of (2S,3S)-methylcitric acid (1) catalysed by citrate (si)-synthase occurs with inversion of configuration in the propionyl moiety; the absolute configurations of the methylcitric acids 1 and 2 indicate a si attack on oxaloacetate. Deuterium in the pro-S position is exchanged for protium 60 times faster than deuterium in the pro-R position. Experiments with (R,S)-(2-2H1)propionyl-CoA allowed the determination of isotope effects. For the enzymatic formation of 1, a primary deuterium isotope effect kH/kD = 1.8 and a secondary alpha-deuterium isotope effect kH/kD = 0.99 were calculated; both are effects on Vmax/KM.